US9023590B2 - Deep-ultraviolet chemically-amplified positive photoresist - Google Patents
Deep-ultraviolet chemically-amplified positive photoresist Download PDFInfo
- Publication number
- US9023590B2 US9023590B2 US14/067,186 US201314067186A US9023590B2 US 9023590 B2 US9023590 B2 US 9023590B2 US 201314067186 A US201314067186 A US 201314067186A US 9023590 B2 US9023590 B2 US 9023590B2
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- US
- United States
- Prior art keywords
- positive photoresist
- cyclopentenyl
- divinyl ether
- pimaric acid
- photoresist according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- SDYAPDAOWDTMAJ-UHFFFAOYSA-N CC(C)C1=CC23CCC4C(C)(C(=O)O)CCCC4(C)C2CC1C1(OC=O)CCCC31 Chemical compound CC(C)C1=CC23CCC4C(C)(C(=O)O)CCCC4(C)C2CC1C1(OC=O)CCCC31 SDYAPDAOWDTMAJ-UHFFFAOYSA-N 0.000 description 4
- FTHROIPJNCRBDX-UHFFFAOYSA-N CC(C)C(C(C1)C2(C3CCC2)C(O)=O)=CC3(CC2)C1C(C)(CCC1)C2C1(C)C(O)=O Chemical compound CC(C)C(C(C1)C2(C3CCC2)C(O)=O)=CC3(CC2)C1C(C)(CCC1)C2C1(C)C(O)=O FTHROIPJNCRBDX-UHFFFAOYSA-N 0.000 description 1
- XLFHQMBKVHJLTL-UHFFFAOYSA-N CC(C)C1=CC23CCC4C(C)(C(=O)O)CCCC4(C)C2CC1C1(OC=O)CCCC31.CC(C)C1=CCC2C(=C1)CCC1C(C)(C(=O)O)CCCC21C.O=C(O)C1=CCCC1 Chemical compound CC(C)C1=CC23CCC4C(C)(C(=O)O)CCCC4(C)C2CC1C1(OC=O)CCCC31.CC(C)C1=CCC2C(=C1)CCC1C(C)(C(=O)O)CCCC21C.O=C(O)C1=CCCC1 XLFHQMBKVHJLTL-UHFFFAOYSA-N 0.000 description 1
Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/28—Unsaturated compounds polycyclic
- C07C61/29—Unsaturated compounds polycyclic having a carboxyl group bound to a condensed ring system
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/0285—Silver salts, e.g. a latent silver salt image
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
- G03F7/0295—Photolytic halogen compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/38—Treatment before imagewise removal, e.g. prebaking
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
- H01L21/0275—Photolithographic processes using lasers
-
- C07C2103/90—
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/90—Ring systems containing bridged rings containing more than four rings
Definitions
- the present invention relates to the field of photosensitive materials, and in particular, to a deep-ultraviolet chemically-amplified positive photoresist.
- a chemically amplified resist it is generally consisted of a photoacid generator (PAG) and an acid-sensitive film-forming resin, and during exposure, the photoacid generator is decomposed to generate a strong acid, which catalyzes the decomposing or crosslinking of the acid-sensitive resin, and because a catalyst may be used circularly in the reaction, the efficiency will be very high.
- the 248 nm photoresist is a resist to which the concept of “chemical amplification” is first applied; and usually, a derivative of poly(para-hydroxystyrene) is employed as the film-forming resin, and an aryliodonium salt or an arylsulfonium salt is employed as the photoacid generator.
- the film-forming resin should have a high transparency at 248 nm; poly(para-hydroxystyrene) and the derivatives thereof have a good transparency at 248 nm themselves, but if impurities are contained in the polymer, the transparency of the resin will be lowered greatly, thus this kind of photoresist has a strict requirement on the purity of poly(para-hydroxystyrene), and the manufacturing process is complex.
- One object of the invention is to provide a deep-ultraviolet chemically-amplified positive photoresist with a good sensitivity.
- the deep-ultraviolet chemically-amplified positive photoresist according to the invention comprises a cyclopentenyl pimaric acid, a divinyl ether, a photoacid generator and an organic solvent, wherein the cyclopentenyl pimaric acid is represented by the following formula:
- the divinyl ether is at least one selected from ethylene glycol divinyl ether, propylene glycol divinyl ether, butylene glycol divinyl ether, diethylene glycol divinyl ether, 1,3-di-(ethyleneoxy ethoxy)benzene, 1-methyl-1,2-diethyleneoxy ethane and 1,7-di-(ethyleneoxy ethoxy)naphthalene, and more preferably, the divinyl ether is ethylene glycol divinyl ether, propylene glycol divinyl ether, diethylene glycol divinyl or, 1,3-di-(ethyleneoxy ethoxy)benzene.
- the photoacid generator is at least one selected from triphenylsulfonium trifluoromethanesulphonate, S-(2-naphthoyl)methyltetrahydrothiophenium trifluoromethanesulphonate, tri(4-methylphenyl)sulfonium trifluoromethanesulphonate, heptafluoropropane sulphonate, (4-methylphenyl)diphenyl trifluoromethanesulphonate, (p-tert-butylphenyl)diphenylsulfonium trifluoromethanesulphonate and tri(p-tert-butylphenyl)sulfonium trifluoromethanesulphonate, and more preferably, the photoacid generator is triphenylsulfonium trifluoromethanesulphonate.
- the organic solvent is at least one selected from acetone, methylethylketone, cyclohexanone, ethylene glycol monoethyl ether, ethylene glycol monoacetate, diethylene glycol, propylene glycol, propylene glycol monoacetate, methyl lactate, propylene glycol methyl ether acetate and ethylene glycol methyl ether acetate.
- the mole ratio of the cyclopentenyl pimaric acid to the divinyl ether is in the range of from about 5:4 to about 1:2, and more preferably, in the range of from about 1:1 to about 2:3.
- the photoacid generator is in the range of from about 0.5% to about 5% by mass of the total mass of the cyclopentenyl pimaric acid and the divinyl ether, and more preferably, in the range of from about 1.0% to about 3.0%.
- the total mass of the photoacid generator, the cyclopentenyl pimaric acid and the divinyl ether is in the range of from about 10% to about 35% by mass of the organic solvent, and more preferably, in the range of from about 10% to about 30%.
- the cyclopentenyl pimaric acid is prepared according to the process which comprises the following steps:
- the detergent is at least one selected from the group consisting of carbon tetrachloride, trichloromethane, acetone, cyclohexanone and ether.
- Another object of the invention is to provide a cyclopentenyl pimaric acid.
- the softening temperature of the cyclopentenyl pimaric acid is in the range of from about 130° C. to about 132° C., and the acid number is about 295 mg KOH/g.
- a diacid with a large alicyclic ring structure i.e., cyclopentenyl pimaric acid
- D-A Diels-Alder
- a deep-ultraviolet chemically-amplified positive photoresist can consist of the cyclopentenyl pimaric acid according to the invention, the divinyl ether and the photoacid generator.
- the deep-ultraviolet chemically-amplified positive photoresist has a good sensitivity.
- a gum resin is added to a four-necked flask equipped with a stirring unit and a condensing unit and heated to a temperature of from about 210 to about 250° C. while a nitrogen gas is introduced into the four-necked flask. Then cyclopentenecarboxylic acid is added dropwise slowly, and the adding time is controlled in the range of from about 2 hours to about 5 hours. After adding of cyclopentenecarboxylic acid is completed, the mixture is continued to react at the temperature of from about 210° C. to about 250° C. for about 3-5 hours. A crude product of cyclopentenyl pimaric acid is obtained after cooling down and discharging from the flask.
- the product is washed for one or more times with a detergent, and preferably, the detergent is at least one selected from the group consisting of carbon tetrachloride, trichloromethane, acetone, cyclohexanone and ether, and then a final product, i.e., cyclopentenyl pimaric acid, is obtained.
- a detergent is at least one selected from the group consisting of carbon tetrachloride, trichloromethane, acetone, cyclohexanone and ether, and then a final product, i.e., cyclopentenyl pimaric acid, is obtained.
- the softening temperature is in the range of from about 130° C. to about 132° C.
- the acid number is about 295 mg KOH/g.
- the content of the target product measured by High Performance Liquid Chromatography (HPLC) is about 75% by mass.
- cyclopentenyl pimaric acid may react with divinyl ether under a heated condition (above 80° C.)., and the resultant product is indissoluble in the dilute alkaline solution.
- the product thus produced may be decomposed rapidly at a temperature higher than 100° C. under the catalysis of a strong acid generated by a photoacid generator, so that it becomes dissoluble in the dilute alkaline solution.
- a positive photoresist can be made of the diacid, the divinyl ether and the acid generator.
- Ethylene glycol divinyl ether (EGDE), propylene glycol divinyl ether (PGDE), butylene glycol divinyl ether (BGDE), diethylene glycol divinyl ether (DEGDE), 1,3-di-(ethyleneoxy ethoxy)benzene (1,3-DEEB), 1-methyl-1,2-diethyleneoxy ethane (1-M-1,2-DE) and 1,7-di-(ethyleneoxy ethoxy)naphthalene (1,7-DEN), etc.
- the above divinyl ethers may be used singly or in a combination of two or more.
- Optional Photoacid Generator Any substance, which is typically used in the traditional chemically-amplified photoresist as an acid generator, may be used as the acid generator in the present invention, and preferred acid generators comprise triphenylsulfonium trifluoromethanesulphonate, S-(2-naphthoyl)methyltetrahydrothiophenium trifluoromethanesulphonate, tri(4-methylphenyl)sulfonium trifluoromethanesulphonate, heptafluoropropane sulphonate, (4-methylphenyl)diphenyl trifluoromethanesulphonate, (p-tert-butylphenyl)diphenylsulfonium trifluoromethanesulphonate and tri(p-tert-butylphenyl)sulfonium trifluoromethanesulphonate, etc., and the above acid generators may be used singly or in a combination of two or more.
- the organic solvent may be any solvent in which the components of a photoresist can be dissolved to generate a homogeneous solution.
- the preferred solvents comprise acetone, methylethylketone (MEK), cyclohexanone (CH), ethylene glycol monoethyl ether (EGME), ethylene glycol monoacetate (EGMA), diethylene glyol (DEG), propylene glycol (PG), propylene glycol monoacetate (PGMA), methyl lactate (ML), propylene glycol methyl ether acetate (PGMEA) and ethylene glycol methyl ether acetate (EGMEA), etc., and the above solvents may be used singly or in a combination of two or more.
- MEK methylethylketone
- CH cyclohexanone
- EGME ethylene glycol monoethyl ether
- EGMA ethylene glycol monoacetate
- DEG diethylene glyol
- PG propylene
- a positive photoresist will be prepared according to the composition listed in the table 1 below.
- the conventional photoetching steps are carried out as follows, wherein the cyclopentenyl pimaric acid used in examples 1-8 is obtained in the synthesization example 1, the cyclopentenyl pimaric acid used in examples 9-11 is obtained in the synthesization example 2, and the cyclopentenyl pimaric acid used in examples 12-13 is obtained in the synthesization example 3:
- a photoresist is coated on a substrate, for example, a silicon wafer, via a spin coater to form a photoresist layer, and then it is prebaked at 60° C. for 90 seconds;
- the photoresist is exposed under a mask plate with a preset pattern, and it is post-baked at 100° C. for 2 minutes after being exposed on the deep-ultraviolet of 248 nm.
- the photoresist coating layer exposed is developed, and a 0.38 wt % tetramethyl ammonium hydroxide is used as the liquid developer, the temperature of the liquid developer is 25° C., and the developing time is 60 seconds.
- the dosages of the cyclopentenyl pimaric acid and the divinyl ether are represented by mass. After being calculated, the mole ratios thereof all fall into the range of 5:4-1:2, and even the preferable range 1:1-2:3.
- the sensitivity of the positive photoresist according to the invention is in the range of from about 18 to about 42 mJ/cm ⁇ 2 , which exhibits a good sensitivity. Therefore, it can be appreciated that the positive photoresist according to the present invention has a good transparency in the deep-ultraviolet band.
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- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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CN201210429479 | 2012-10-31 | ||
CN201210429479.1 | 2012-10-31 | ||
CN201210429479.1A CN102929102B (zh) | 2012-10-31 | 2012-10-31 | 一种深紫外化学增幅型正性光致抗蚀剂 |
Publications (2)
Publication Number | Publication Date |
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US20140120474A1 US20140120474A1 (en) | 2014-05-01 |
US9023590B2 true US9023590B2 (en) | 2015-05-05 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US14/067,186 Active 2033-11-30 US9023590B2 (en) | 2012-10-31 | 2013-10-30 | Deep-ultraviolet chemically-amplified positive photoresist |
Country Status (5)
Country | Link |
---|---|
US (1) | US9023590B2 (zh) |
EP (1) | EP2728408B1 (zh) |
JP (1) | JP6169478B2 (zh) |
KR (1) | KR101564808B1 (zh) |
CN (1) | CN102929102B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014092792A (ja) * | 2012-10-31 | 2014-05-19 | Boe Technology Group Co Ltd | 深紫外線化学増幅型ポジ型フォトレジスト |
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US5480762A (en) * | 1990-11-28 | 1996-01-02 | Fuji Photo Film Co., Ltd. | Method for preparing lithographic printing plate |
US6265131B1 (en) | 2000-04-03 | 2001-07-24 | Everlight Usa. Inc. | Alicyclic dissolution inhibitors and positive potoresist composition containing the same |
US20020031719A1 (en) | 2000-07-14 | 2002-03-14 | Tokyo Ohka Kogyo Co., Ltd. | Novel copolymer, photoresist composition, and process for forming resist pattern with high aspect ratio |
CN1407406A (zh) | 2001-08-15 | 2003-04-02 | 希普雷公司 | 光刻胶组合物 |
JP2005010213A (ja) | 2003-06-16 | 2005-01-13 | Tokyo Ohka Kogyo Co Ltd | 化学増幅型ポジ型ホトレジスト組成物およびレジストパターンの形成方法 |
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CN102156385A (zh) | 2011-05-19 | 2011-08-17 | 北京师范大学 | 含2,1,4-重氮萘醌磺酸酚酯的化学增幅型i-线正性光致抗蚀剂组合物 |
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JPH11258804A (ja) * | 1998-03-09 | 1999-09-24 | Fuji Photo Film Co Ltd | ポジ型感光性組成物 |
JP4031593B2 (ja) * | 1999-04-13 | 2008-01-09 | 太陽インキ製造株式会社 | ポジ型感光性樹脂組成物 |
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CN102929102B (zh) * | 2012-10-31 | 2014-05-21 | 京东方科技集团股份有限公司 | 一种深紫外化学增幅型正性光致抗蚀剂 |
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2012
- 2012-10-31 CN CN201210429479.1A patent/CN102929102B/zh active Active
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2013
- 2013-10-28 EP EP13190478.1A patent/EP2728408B1/en active Active
- 2013-10-30 US US14/067,186 patent/US9023590B2/en active Active
- 2013-10-31 KR KR1020130131087A patent/KR101564808B1/ko active IP Right Grant
- 2013-10-31 JP JP2013227035A patent/JP6169478B2/ja active Active
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US5480762A (en) * | 1990-11-28 | 1996-01-02 | Fuji Photo Film Co., Ltd. | Method for preparing lithographic printing plate |
US6265131B1 (en) | 2000-04-03 | 2001-07-24 | Everlight Usa. Inc. | Alicyclic dissolution inhibitors and positive potoresist composition containing the same |
US20020031719A1 (en) | 2000-07-14 | 2002-03-14 | Tokyo Ohka Kogyo Co., Ltd. | Novel copolymer, photoresist composition, and process for forming resist pattern with high aspect ratio |
CN1407406A (zh) | 2001-08-15 | 2003-04-02 | 希普雷公司 | 光刻胶组合物 |
CN1701280A (zh) | 2003-05-22 | 2005-11-23 | 东京应化工业株式会社 | 化学放大型正性光致抗蚀剂组合物以及形成抗蚀剂图案的方法 |
JP2005010213A (ja) | 2003-06-16 | 2005-01-13 | Tokyo Ohka Kogyo Co Ltd | 化学増幅型ポジ型ホトレジスト組成物およびレジストパターンの形成方法 |
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Chinese Office Action and translation regarding Application No. 201210429479 dated Aug. 13, 2013. Translation provided by Dragon Intellectual Property Law Firm. |
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Extended European Search Report regarding Application No. 13190478.1-1564, dated Feb. 6, 2014. |
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Werner Herz et al "Resin acids, XIX, Structure and sterochemistry of adducts of levopimaric acid with cyclopentenone and 1-cyclepentene-3, 5-dione. Favorski reaction of an enedione epoxide", The Journal of Organic Chemistry, vol. 34, No. 12, Dec. 1, 1969, pp. 4016-4023. |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014092792A (ja) * | 2012-10-31 | 2014-05-19 | Boe Technology Group Co Ltd | 深紫外線化学増幅型ポジ型フォトレジスト |
Also Published As
Publication number | Publication date |
---|---|
EP2728408A1 (en) | 2014-05-07 |
JP2014092792A (ja) | 2014-05-19 |
CN102929102B (zh) | 2014-05-21 |
JP6169478B2 (ja) | 2017-07-26 |
KR20140056108A (ko) | 2014-05-09 |
EP2728408B1 (en) | 2015-07-15 |
US20140120474A1 (en) | 2014-05-01 |
CN102929102A (zh) | 2013-02-13 |
KR101564808B1 (ko) | 2015-10-30 |
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